Technically, I've done as you've described several times over. Did it with IOS and Android - I approached both with an open wallet and open to doing things differently than I was used to. Could say the same for several gaming consoles and Chrome. ALL have required concessions on my part that left a bad taste in my mouth - speaking strictly from a User Experience perspective.
The worst of it has been all the apps that dissappeared from the IOS Appstore - apps I paid for and now all that's available are pale imitations full of ads and demanding subscriptions.
I'm not asking the same apps to work across multiple decades either - the gap between my first iPad and my second was less than eight years.